Chemical reactions of 8-quinolinol derivatives and their applications to biochemical tools and enzyme inhibitors

Shin Aoki, Shinya Ariyasu, Kengo Hanaya, Yosuke Hisamatsu, Takeshi Sugai

Research output: Contribution to journalReview article

1 Citation (Scopus)

Abstract

8-Quinolinol (8-hydroxyquioline, 8HQ) attracts much attention in material sciences and biorelated sciences, because of their simple structures, strong metal coordination properties, fluorescence properties, and extensive possibility of functionalization. In this review, five applications of 8HQ are described. The first application is 8HQ-linked macrocyclic tetraamines as fluorescent probes of zinc ions in living cell. The second and third sections provide the applications of 8HQ to inhibitors against dinuclear zinc hydrolase and to radioprotectors that can inhibit apoptosis of radiosensitive normal cells during radiotherapy. In the third section, finding of photochemical S-O bond cleavage reaction of 8HQ sulfonates (8HQS) under aqueous conditions, its mechanistic analysis and applications to photocleavable chemical linkers are described. Finally, the photophysical properties of iridium (III) complexes having 8HQ or its analogs will be presented. This knowledge will be useful in design and synthesis of useful molecules containing 8HQ units, in bioorganic chemistry, chemical biology, pharmaceutical science, material science, and other related scientific fields.

Original languageEnglish
Pages (from-to)482-493
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume74
Issue number5
Publication statusPublished - 2016

Fingerprint

Oxyquinoline
Enzyme Inhibitors
Chemical reactions
Derivatives
Materials science
Zinc
Iridium
Radiotherapy
Hydrolases
Fluorescent Dyes
Metals
Fluorescence
Cells
Ions
Apoptosis
Molecules
Pharmaceutical Preparations

Keywords

  • 8-Quinolinol
  • Biotin linker
  • Luminescent metal complexes
  • Metal enzyme inhibitors
  • Metal ion probes
  • Photolysis reactions
  • Radioprotective agents

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Chemical reactions of 8-quinolinol derivatives and their applications to biochemical tools and enzyme inhibitors. / Aoki, Shin; Ariyasu, Shinya; Hanaya, Kengo; Hisamatsu, Yosuke; Sugai, Takeshi.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 74, No. 5, 2016, p. 482-493.

Research output: Contribution to journalReview article

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